Ultra violet, violet, and blue light filtering polymers for ophthalmic applications

ABSTRACT

Opthalmic devices, particularly intraocular lenses (IOL), with improved contrast sensitivity and methods of making same. In one aspect, blue light blocking chromophores (BLBC) are diffused into, e.g. an IOL lens body to create a BLBC gradient in the lens. Orange dyes are preferred BLBCs.

FIELD OF INVENTION

This invention relates to ophthalmic devices or apparatuses,particularly intraocular lenses (IOLS), with improved contrastsensitivity and protection from UV, violet, and blue light. Thisinvention is particularly applicable to acrylic foldable IOLs andcontact lenses. Novel methods of making ophthalmic devices also aredisclosed.

BACKGROUND OF THE INVENTION

The assessment of optical hazards in recent years has led to therecognition of the possible hazards to the retina associated with bluelight. Generally speaking blue light has a wavelength in the range ofabout 400-500 nm. If the blue light hazard is a real threat to vision,then the UV/visible transmission characteristics of ophthalmic lenses,and intraocular lenses (IOLs) in particular, should be modified toprovide adequate protection from blue light hazards encountered in theenvironment.

In the ambient environment, solar radiation is the primary visionhazard. The sun freely emits UV, visible and IR radiation much of whichis absorbed by the atmosphere. The solar radiation that is transmittedthrough the atmosphere and reaches the earth's surface consists of UV-Bradiation (230-300 nm), near UV or UV-A radiation (300-400 nm), visiblelight (400-700 nm) and near IR radiation (700-1400 nm). The ocular mediaof man in its normal, healthy state freely transmits near IR and most ofthe visible spectrum to the retina. UV-B radiation is, however, absorbedby the cornea and does not reach the retina. UV-A and the blue portionof the visible spectrum can be absorbed by the crystalline lens of theeye depending upon the person's age.

The human crystalline lens changes its UV and visible transmissioncharacteristics as it ages. In infancy the human lens will freelytransmit near UV and visible light above 300 nm, but with further agingthe action of UV radiation from the environment causes the production ofyellow pigments, called fluorogens, within the lens. By approximatelythe age of 54 the lens will not significantly transmit light below 400nm and the transmission of light between 400 and 500 nm is greatlydiminished. As the lens ages it continuously develops a yellow color,increasing its capacity to filter out near UV violet, and blue light.

Currently, IOLs capable of blocking UV and blue light to varying degreesuse yellow dyes. However, there are some major drawbacks with such IOLs:

-   -   1. Patients with yellow dye-containing IOLs experience reduced        vision quality in dim light conditions. The yellow dyes used in        current IOLs absorb light over of a relatively large band of        wavelengths and a higher concentration is needed to achieve        adequate blue light filtration. This causes a shift of        absorption from the UV-violet-blue (200-420 nm) to the green        region (420-470 nm).    -   2. The presence of blue light blocking chromophore in e.g.,        IOLs, reduces contrast sensitivity in some cases.

Due to their intense yellow color (which the presence of blue lightchromophores imparts to IOLs), blue light blocking chromophores in IOLsand other ophthalmic devices may interfere with color perception.

SUMMARY OF THE INVENTION

The present invention, in one aspect, is the use of a chromophore (dyes)or a combination of chromophores to optimize UV, violet, and blue lightfiltering of polymeric ophthalmic devices, particularly IOLs. It hasbeen discovered that using one or more selected chromophores, withspecific wavelength absorptions, and low concentrations, affordsophthalmic devices specifically including but not limited to, IOLs, moreparticularly described below, with improved light transmissioncharacteristics.

Thus, in one embodiment, the present invention comprises an ophthalmicdevice, which includes polymerizable orange chromophores. Preferredpolymerizable orange chromophores include but are not limited to:disperse orange 3 acrylamide, disperse orange 3 methacrylamide, disperseorange 3 acrylate, disperse orange 3 methacrylate, disperse orange 25acrylamide, disperse orange 25 methacrylamide, disperse orange 25acrylate, disperse orange 25 methacrylate, and 10-Dodecylacridine OrangeBromide. Other orange chromophores include but are not limited to:

ACID ORANGE 12 (CROCEINE ORANGE C.I. 15970) ACID ORANGE 128 (MERPACYLORANGE R) (1) ACID ORANGE 132 (MERPACYL YELLOW AR) ACID ORANGE 19(SUPRAMINE RED GGA) ACID ORANGE 2 B (1) ACID ORANGE 3 (C.I. 10385) (1)ACID ORANGE 33 (C.I. 24780) (1) ACID ORANGE 34 (CHROMACYL ORANGE GR) (1)ACID ORANGE 43 (XYLENE FAST ORANGE P) (1) ACID ORANGE 47 (BENZYL FASTORANGE G) (1) ACID ORANGE 5 (ACID YELLOW D C.I. 13080) (1) ACID ORANGE51 (1) ACID ORANGE 60 (CAPRACYL ORANGE R) (1) ACID ORANGE 62 (NEOLANORANGE GRE) (1) ACID ORANGE 63 ACID ORANGE 63 (POLAR YELLOW R ORSUPRANOL YELLOW RA) (1) ACID ORANGE 64 (CAPRACYL YELLOW 3 RD) (1) ACIDORANGE 74 (1) ACID ORANGE 74 (NEOLAN ORANGE G OR GYCOLAN ORANGE GL) (1)ACID ORANGE 79 (C.I. 23255) (1) ACID ORANGE 8 (1) ACID ORANGE 86(IRGALAN ORANGE RL) (1) ACID ORANGE 87 (CIBALAN YELLOW 2 BRL) (1) ACIDORANGE 94 (IRGANOL ORANGE GRLS) (1) ACID ORANGE CAPRACYL BROWN HRN (1)ACID ORANGE GG CRYSTALS (1) ACRIDINE ORANGE 10-NONYL BROMIDE (2) AMANILFAST ORANGE ER (1) AMIDINE FAST ORANGE 2 RL (1) ANTHANOL CHROME ORANGE R(1) ASTRAZON ORANGE G (1) ASTRAZON ORANGE R (1) AZOANTHRENE GOLDENORANGE R (1) BASIC ORANGE 21 (GENACRYL ORANGE G) (1) BASIC ORANGE 22(GENACRYL ORANGE R) (1) BASIC ORANGE 24 (SEVRON ORANGE L) (1) BASICORANGE 25 (SEVRON ORANGE CL) (1) BASIC ORANGE 26 (SEVRON BROWN YL) (1)BASIC ORANGE 27 (ASTRAZON ORANGE 3 RL) (1) BASIC ORANGE 28 (ASTRAZONORANGE RRL) (1) BASIC ORANGE 29 (ASTRAZON GOLDEN YELLOW GLD) (1) BASICORANGE 30 (ASTRAZON YELLOW BROWN 2 GL) (1) BASIC ORANGE 4-11(C.I. 46035)(1) BASIC ORANGE 43 (DEORLENE FAST ORANGE 2 GL) (1) BASIC ORANGE 54(MAXILON ORANGE 4 RL EXTRA CONC.) (1) BENZANOL ORANGE R (1) BENZO FASTORANGE 2 RL (1) BENZO FAST ORANGE WS (1) BENZYL ORANGE (1) BROMOCRESOLORANGE (1) BUFFALO DIRECT ORANGE Y (1) C.I. 326 AMANIL FAST ORANGE S (1)C.I. 621 AMANIL FAST ORANGE CG (1) CALCO ACID ORANGE II (1) CALCOCHROMEORANGE R EXTRA CONC. (1) CALCOCID FAST LIGHT ORANGE 2 G (1) CALCOCIDMILLING ORANGE 4 R CONC. (1) CALCOCID ORANGE Y EXTRA CONC. (1) CALCODURORANGE EGL (1) CALCODUR ORANGE GL (1) CALCOFAST WOOL ORANGE 4 RN (1)CALCOFORM ORANGE 5 RE (1) CALCOLITE FAST ORANGE 3 R (1) CALCOLOIDFLAMING ORANGE 6 RD EXTRA CONC. (1) CALCOLOID GOLDEN ORANGE 4 RD (1)CALCOLOID GOLDEN ORANGE GD EXTRA CONC. (1) CALCOLOID GOLDEN ORANGE RRTDEXTRA CONC. (1) CALCOLOID ORANGE RD EXTRA CONC. (1) CALCOMET ORANGE G(1) CALCOMINE FAST ORANGE 2 RS EXTRA (1) CALCOMINE FAST ORANGE E3G (1)CALCOMINE FAST ORANGE EG (1) CALCOMINE FAST ORANGE ER (1) CALCOMINEORANGE 2RS (1) CALCOMINE ORANGE R SPECIAL (1) CALCONESE BRILLIANT ORANGEGF CONC. (1) CALCONESE ORANGE 3 RC (1) CALCONESE ORANGE G (1) CALCOSOLGOLDEN ORANGE RRTP (1) CALCOSOL PRINTING ORANGE RY (1) CALCOZINE ORANGERS (1) CALCOZINE ORANGE YC (1) CAMACYL BRILLIANT ORANGE JER (1) CAPRACYLORANGE RP (1) CELACYL BRILLIANT ORANGE 3 R (1)-HYDROXY-1,4-NAPHTHOQUINONE (1) CHRYSOIDINE G (2) SUDAN II (1)TROPAEOLIN 000 NO. 1 (1) TROPAEOLIN O (1) TROPAEOLIN O SODIUM SALT (1)TROPAEOLIN OO (1) THIOXINE ORANGE R (1) TOLUYLENE FAST ORANGE LX (1)VARINYL ORANGE DAC (1) VAT ORANGE 1 (C.I. 59105) (1) VAT ORANGE 24(PONSOL GOLDEN ORANGE 3 GND EXTRA) (1) VAT ORANGE 3 (C.I. 59300) (1) VATORANGE 7 (SOLANTHRENE BRILLIANT ORANGE FJRA) (1) VAT ORANGE 9 (C.I.59700) (1) VEGENTINE ORANGE CSW (1) VERANTHRENE GOLDEN ORANGE 3 G (1)SUDAN ORANGE G (2) SULFONINE ORANGE GS CONC. (1) SULPHUR ORANGE (1)SUPERLITE FAST ORANGE RT (1) SUPRAMINE ORANGE G (1) SUPRANOL ORANGE RA(1) TANNIN ORANGE (1) TECTILON ORANGE 2 RT (1) THIAZOLE ORANGE (2)SOLVENT ORANGE 1 (NEWPORT OIL YELLOW C.I. 11920) (1) SOLVENT ORANGE 20(AZOSOL FAST ORANGE RA) (1) SOLVENT ORANGE 23 (IOSOL ORANGE) (1) SRAGOLDEN ORANGE FSI POWDER (1) SRA GOLDEN ORANGE I POWDER (1) SRA LIGHTORANGE FSI (1) SRA ORANGE BL (1) SRA ORANGE I POWDER (1) SRA ORANGE IIPOWDER SODIUM4-(3-(2,4-DI-ME-PH-AZO)-2,4-DI-HO-PH-AZO)-BENZENESULFONATE(ACID ORANGE24 (1) SODIUM4-(4-(BENZYL-ET-AMINO)-PH-AZO)-2,5-DI-CL-BENZENESULFONATE(ACID ORANGE50) (1) SODIUM 5-(4-CL-PH-AZO)-6-HO-NAPHTHALENE-2-SULFONATE(ACID ORANGE31 C.I. 15995) (1) SOLOPHENYL ORANGE TGL (1) REACTIVE ORANGE 5 (CIBACRONBRILLIANT ORANGE GP) (1) REACTIVE ORANGE 68 (LANASOL ORANGE R) (1)REACTIVE ORANGE 70 (CIBACRON GOLDEN YELLOW RE) (1) REACTONE ORANGE G (1)RESIST ORANGE N (1) RESOLIN ORANGE 5 R (1) RORACYL ORANGE R (1)ROSANTHRENE ORANGE 3 R CONC. (1) ROSANTHRENE ORANGE RSS (1) SETACYLORANGE P-RFL (1) REACTIVE ORANGE 13 (PROCION ORANGE H-2R) (1) REACTIVEORANGE 16 (1) REACTIVE ORANGE 2 (CIBACRON BRILLIANT ORANGE 2G-E) (1)REACTIVE ORANGE 29 (LANASOL ORANGE G) (1) REACTIVE ORANGE 35 (CIBACRONORANGE 4 R-A) (1) REACTIVE ORANGE 44 (CIBACRON PRONT ORANGE G) (1)REACTIVE ORANGE 45 (CIBACRON PRONT GOLDEN YELLOW 2 R) (1) REACTIVEORANGE 46 (CIBACRON PRONT ORANGE BROWN 3 R) (1) PONTAMINE FAST ORANGE 2G CONC. (1) PONTAMINE FAST ORANGE MR (1) PONTAMINE FAST ORANGE MRL (1)PONTAMINE FAST ORANGE RGL EXTRA CONC. (1) PONTAMINE FAST ORANGE S (1)PROCION ORANGE MX2R (1) PROCION ORANGE MXG (1) PYRAMINE ORANGE 3 G (1)PYRAMINE ORANGE R (1) PYRAZOL FAST ORANGE RL (1) POLYDYE HISPERSE ORANGE5 RH (1) POLYFORM ORANGE RF EXTRA CONC. (1) POLYPROPYLENE ORANGE Y (1)PONSOL BRILLIANT ORANGE RKD EXTRA CONC. (1) PONSOL GOLDEN ORANGE 4 RDEXTRA CONC. (1) PONSOL GOLDEN ORANGE G EXTRA CONC. (1) PONSOL GOLDENORANGE GD EXTRA CONC. (1) PONSOL GOLDEN ORANGE RRTD EXTRA CONC. (1)PONTACHROME ORANGE 4 G (1) PONTACHROME ORANGE RL (1) PARA BRILLIANTORANGE G (1) PARANOL FAST ORANGE EG (1) PARANOL FAST ORANGE ER (1)PARANOL FAST ORANGE GL (1) POLAR ORANGE R CONC. (1) POLY(DISPERSE ORANGE3 ACRYLAMIDE) (1) POLY(DISPERSE ORANGE 3 METHACRYLAMIDE) (1) POLY[METHYLMETHACRYLATE-CO-(DISPERSE ORANGE 3 ACRYLAMIDE)](1) POLY[METHYLMETHACRYLATE-CO-(DISPERSE ORANGE 3 METHACRYLAMIDE)](1) ORANGE G (5)ORANGE G SOLUTION (1) ORANGE GG (1) ORANGE GS (1) MORDANT ORANGE 34(CHROMAVEN BRILLIANT ORANGE 2 R) (1) MORDANT ORANGE 8 (OMEGA CHROMEORANGE ML) (1) NABOR ORANGE G (1) NABOR ORANGE R (1) NAPTHANIL ORANGE RBASE (1) NATIONAL CHROMOLAN ORANGE R (1) NATIONAL WOOL ORANGE A CONC.(1) NATURAL YELLOW 8, 11 (ANRANTINE OSAGE ORANGE C.I. 75660) (1)NEUTRACYL ORANGE R (1) NEUTRAL ORANGE O (1)

Generally speaking, any polymerizable orange dye may be used in thisembodiment of this invention. “Orange dye” for purposes of thisinvention includes polymerizable dyes having a coefficient of extinction“e” of at least 1500 M-¹cm-¹, preferably 3000 M-¹cm-¹, and mostpreferably 5000 M-¹cm-¹ for the region between 350 nanometers (nm) and500 nm. Coefficients of distinction would, of course, be well known toone skilled in the art.

In a further embodiment, the present invention includes polymericophthalmic devices which comprise orange dyes or orange chromophores asset forth above and include an ethylenically unsaturated anthracenemoiety e.g., vinyl anthracene.

In yet a further embodiment, the present invention comprises polymericophthalmic devices comprising orange chromophores or dyes as set forthabove and substituted hydroxybenzophenones and substitutedhydroxybenzotriazoles. Preferred benzophenones include the2-hydroxybenzophenones disclosed in U.S. Pat. No. 4,304,895. Whilepreferred benzotriazoles include the2-hydroxy-5-acryloxyphenyl-2H-benzotriazoles disclosed in U.S. Pat. No.4,528,311, both said patents being incorporated by reference herein. Amost preferred ultraviolet-absorbing compound in this family is2-3′-methallyl-2′-hydroxy-5′ methyl phenyl benzotriazole.

In one variation of this invention, polymerizable orange dyes orchromophores are created or synthesized from non-polymerizable orangedyes by derivatizing the orange dye, e.g., to add a polymerizationfunctionality. In one embodiment of this variation, a non-polymerizableorange dye is reacted with a selected species to add a site of ethylenicor vinylic unsaturation, i.e., double bond functionality. A suitableorange dye may be modified to add multiple reaction sites. Reactionsites, other than free-radically polymerizable sites, also may be addedor created depending upon dye characteristics.

One skilled in the art will appreciate that the polymerizable orange dyeis the resulting product of the derivatization reaction. Put otherwise,a polymerizable orange dye must be produced from the derivatizationreaction but need not be an orange dye starting material, as definedherein. A dye could become both polymerizable and “orange” as describedherein in a derivatization reaction were the right functionality addedor chemical structure modification made e.g., dehydrogenation of anon-orange dye reactant, starting material. The syntheses described atparagraphs 20, 21, and 22, below illustrate this embodiment of theinvention.

In yet a further embodiment, the present invention comprises polymericophthalmic devices including polymerizable orange chromophores or dyesset forth above and further comprises benzotriazoles, benzophenones, andethylenically unsaturated anthracene moieties, as set forth above. Inessence, a mixture of the classes of chromophores to which the presentinvention related may be used.

One skilled in the art will appreciate that while a present invention isprimarily described in terms of IOLs, there are many ophthalmic deviceswhose characteristics will be enhanced by application of the teaching ofthe present disclosure.

DETAILED DESCRIPTION OF THE INVENTION Ophthalmic Device Base Polymer

Suitable monomers for use in polymeric ophthalmic device of the presentinvention include but are not limited to carbazole and/or naphthylmoiety, carbazole, naphthalene, or a naphthyl group such as vinylcarbazole, vinyl naphthalene, lauryl methacrylate, stearyl methacrylate,methyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethylmethacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate,n-vinyl pyrrolidone, styrene, eugenol (4-hydroxyvinylbenzene),alpha.-methylstyrene. In addition, for high-refractive index foldablelens applications, suitable monomers include, but are not limited to:2-ethylphenoxy methacrylate, 2-ethylphenoxy acrylate, 2-ethylthiophenylmethacrylate, 2-ethylthiophenylacrylate, 2-ethylaminophenylmethacrylate, phenyl methacrylate, benzyl methacrylate, 2-phenylethylmethacrylate, 3-phenylpropyl methacrylate, 4-phenylbutyl methacrylate,4-methylphenyl methacrylate, 4-methylbenzyl methacrylate,2-2-methylphenylethyl methacrylate, 2-3-methylphenylethyl methacrylate,2-4-methylphenylethyl methacrylate, 2-(4-propylphenyl)ethylmethacrylate, 2-(4-(1-methylethyl)phenyl)ethyl methacrylate,2-(4-methoxyphenyl)ethyl methacrylate, 2-(4-cyclohexylphenyl)ethylmethacrylate, 2-(2-chlorophenyl)ethyl methacrylate,2-(3-chlorophenyl)ethyl methacrylate, 2-(4-chloro-phenyl)ethylmethacrylate, 2-(4-bromophenyl)ethyl methacrylate,2-(3-phenylphenyl)ethyl methacrylate, 2-(4-phenylphenyl)ethylmethacrylate), 2-(4-benzylphenyl)ethyl methacrylate, and the like,including the corresponding methacrylates and acrylates. N-vinylpyrolidone, styrene, eugenol and .alpha.-methyl styrene may also besuitable especially for high-refractive index foldable lensapplications.

A preferred lens-forming monomer mixture is the mixture of vinylcarbazole, lauryl methacrylate, and hydroxyethyl acrylate. Conventionalmethods for polymerization of the preferred monomer mixture to apreferred polymeric lens material would be well known to one skilled inthe polymer art.

A copolymerizable cross-linking agent is preferably used in thelens-materials of this invention such cross-linking may be anyterminally or internally ethylenically unsaturated compound having morethan one unsaturated group. Suitable cross-linking agents include, forexample: ethylene glycol dimethacrylate, diethylene glycoldimethacrylate, allyl methacrylate, 1,3-propanediol dimethacrylate,allyl methacrylate, 1,6-hexanediol dimethacrylate, 1,4-butanedioldimethacrylate, and the like. A preferred cross-linking agent isethylene glycol dimethacrylate. Suitable crosslinkers also includepolymeric crosslinkers, such as, polyethylene glycol 1000 diacrylate,polyethylene glycol 1000 dimethacrylate, polyethylene glycol 600dimethacrylate, polybutanediol 2000 dimethacrylate, polypropylene glycol1000 diacrylate, polypropylene glycol 1000 dimethacrylate,polytetramethylene glycol 2000 dimethacrylate, and polytetramethyleneglycol 2000 diacrylate.

Chromophore System

To achieve optimal light transmission and UV, violet, and blue lightblocking, the chromophores described above may be used separately or invarious combinations with concentrations varying from about 0.001% to10% by weight comprises a mixture preferably about 0.002% to about 5% byweight, and most preferably about 0.003% to about 3% by weight. Apreferred formulation contains one or more chromophores selected fromeach of the three classes of chromophores discussed above.

Synthesis of Polymerizable Orange Dyes

Disperse Orange 3 methacrylamide Synthesis

0.6 g of sodium hydride was added carefully to a 3 neck flask equippedwith a condenser, addition funnel, and magnetic bar. 75 ml of anhydrousTHF was added and the mixture stirred for 10 minutes. A solution of 4.0g 4-(4-nitrophenylazo)aniline in 75 ml THF was added drop-wise and theflask stirred at 50° C. The temperature was raised to 95° C., and themixture was refluxed for 6 hrs. The mixture was allowed to cool to roomtemperature and then 6.0 g of methacrylic acid in 20 ml THF was addeddrop-wise. The mixture was again refluxed for 8 hrs. The solution wascooled to room temperature. THF was evaporated to reveal a dark orangesolid. The solid was washed thoroughly with dilute HCl and water. Theproduct was recrystallized in 95% methanol. The yield was 56%.

Disperse Orange 25 Methacrylamide Synthesis

3-[N-Ethyl-4-(4nitrophenylazo)phenylamino]propionitrile was used insteadof 4-(4-nitrophenylazo)aniline in the above procedure. The yield was42%.

Disperse Orange 3 Acrylamide Synthesis

0.6 g of sodium hydride was added carefully to a 3 neck flask equippedwith a condenser, addition funnel, and magnetic bar. 75 ml of methylenechloride was added and the mixture stirred for 10 minutes. A solution of4.0 g 4-(4-nitrophenylazo)aniline in 75 ml methylene chloride was addeddrop-wise and the flask stirred at 50° C. The temperature was raised to95° C., and the mixture was refluxed for 6 hrs. The mixture was allowedto cool to room temperature and then 6.0 g of acrylic acid in 20 mlmethylene chloride was added drop-wise. The mixture was again refluxedfor 8 hrs. The solution was cooled to room temperature. Methylenechloride was evaporated to reveal a dark orange solid. The solid waswashed thoroughly with dilute HCl and water. The product wasrecrystallized in 95% methanol. The yield was 35%.

Disperse Orange 25 Acrylamide Synthesis

3-[N-Ethyl-4-(4nitrophenylazo)phenylamino]propionitrile was used insteadof 4-(4-nitrophenylazo)aniline in the above procedure. The yield was38%.

Commercially available chromophores may in some instances be used. Caremust be taken to remove any residual initiators, processing aids orother extraneous additives, including unpolymerized monomer(s), whichmight not be suitable for long-term exposure to ophthalmic fluid or tothe ophthalmic environment.

Methods of Manufacture General Preparation Steps for Polymers of Example1-10

The comonomers listed below were mixed in a glass flask using a magneticstir bar for at least 30 minutes followed by sonication for 30 minutesat a power setting of 100% on a Branson 5510 and then stirring again foranother 30 minutes. The combination of sonication andhydrophilic/hydrophobic repulsion forces allows the formation ofnanoclusters. AIBN was added at a concentration of 0.2% by weight. Thecomonomer mixture was vacuum degassed and placed in a Teflon tubularmold. The mold was placed in water bath at 70° C. for 12 hours thancured at 100° C. for 12 hours. A polymer rod measuring 19 mm in diameterand 6 inches in length was removed from the mold, cured for 12 hours at100° C. and annealed for 14 hours at 100° C. for further processing. Thepolymer rod was machined into 17 mm×2 mm disks and IOLs were cut fromthe samples.

The refractive index was measured using a CLR 12-70 refractometer fromIndex Instrument. The optical properties of the IOLs were measured byUV/VIS spectroscopy using a DU-50 spectrophotometer from BeckmanInstruments. To assess the efficiency of UV light and blue lightblocking, percent light transmittance was measured at key wavelengthsincluding 400, 420, and 470 nm. A comparative analysis with acommercially available IOL containing a yellow dye (Acrysof Natural®)was included in the studies.

Examples 1-10

% Transmittance Monomer Conc. RI 400 nm 420 nm 470 nm 1. VC 30 1.569 1023 53 LM 37 HEMA 29.5 EGDM 2.92 DOM2 0.08 5 0.5 VA 2. VC 30 1.568 14 2765 LM 36.7 HEA 30 EGDM 2.92 DOA3 0.08 MEB 0.3 3. VC 30 1.563 4 15 54 EHA36.2 HEMA 30 EGDM 2.95 DOM2 0.05 5 0.5 VA 0.3 MEB 4. VC 30 1.562 8 19 65EHA 36.1 HEA 30 EGDM 2.95 DOM3 0.05 VA 0.6 MEB 0.3 5. VN 30 1.554 7 9 54EHA 36.3 HEMA 30 EGDM 2.95 DOM2 0.05 5 0.4 VA 0.3 MEB 6. VC 29 1.551 1 248 EHA 37 HEA 30 EGDM 2.98 DOA3 0.02 VA 1.0

PREFERRED FORMULATIONS 7. VC 21. 1.539 1 19 62 HEA 3 LM 28. EGD 0 M 46.DOM 7 3 2.9 VA 85 MEB 0.0 15 0.7 0.3 8. VC 21. 1.536 1 15 60 HEA 3 LM28. EGD 0 M 46. DOM 7 3 2.9 VA 82 MEB 0.0 18 0.7 0.3 9. VC 21. 1.535 114 50 HEA 3 LM 28. EGD 0 M 46. DOM 7 3 2.9 VA 7 MEB 0.0 3 0.7 0.3 10. VC21. 1.537 1 19 55 HEA 3 LM 28. EGD 0 M 46. DOM 7 3 2.9 VA 8 MEB 0.0 20.7 0.3 Acrysof Natural ® not known 6 28 57 VC: vinyl carbazole VN:2-vinyl naphthalene EHA: 2-ethylhexylacrylate LM: Lauryl methacrylateHEMA; Hydroxyethylmethacrylate HEA: Hydroxyethylacrylate EGDM: ethyleneglycol dimethacrylate VA: vinyl anthracene MEB:2-(2′-Methacryloxy-5′methylphenyl)benzotriazole DOM3: Disperse Orange 3Methacrylamide DOA3: Disperse Orange 3 Acrylamide DOM25: Disperse Orange25 Methacrylamide

The results show that the novel chromophore system provides excellentUV, violet, and blue light filtering without compromising lighttransmission at higher wavelengths.

1-7. (canceled)
 8. A lens comprising a copolymer of an ophthalmic devicebase monomer and a polymerizable orange dye wherein the orange dye isselected from the group consisting essentially of: disperse orange 3acrylamide, disperse orange 3 methacrylamide, disperse orange 3acrylate, disperse orange 3 methacrylate, disperse orange 25 acrylamide,disperse orange 25 methacrylamide, disperse orange 25 acrylate, disperseorange 25 methacrylate, and 10-Dodecylacridine Orange Bromide, ACIDORANGE 12 (CROCEINE ORANGE C.I. 15970) ACID ORANGE 128 (MERPACYL ORANGER) (1) ACID ORANGE 132 (MERPACYL YELLOW AR) ACID ORANGE 19 (SUPRAMINERED GGA) ACID ORANGE 2 B (1) ACID ORANGE 3 (C.I. 10385) (1) ACID ORANGE33 (C.I. 24780) (1) ACID ORANGE 34 (CHROMACYL ORANGE GR) (1) ACID ORANGE43 (XYLENE FAST ORANGE P) (1) ACID ORANGE 47 (BENZYL FAST ORANGE G) (1)ACID ORANGE 5 (ACID YELLOW D C.I. 13080) (1) ACID ORANGE 51 (1) ACIDORANGE 60 (CAPRACYL ORANGE R) (1) ACID ORANGE 62 (NEOLAN ORANGE GRE) (1)ACID ORANGE 63 ACID ORANGE 63 (POLAR YELLOW R OR SUPRANOL YELLOW RA) (1)ACID ORANGE 64 (CAPRACYL YELLOW 3 RD) (1) ACID ORANGE 74 (1) ACID ORANGE74 (NEOLAN ORANGE G OR GYCOLAN ORANGE GL) (1) ACID ORANGE 79 (C.I.23255) (1) ACID ORANGE 8 (1) ACID ORANGE 86 (IRGALAN ORANGE RL) (1) ACIDORANGE 87 (CIBALAN YELLOW 2 BRL) (1) ACID ORANGE 94 (IRGANOL ORANGEGRLS) (1) ACID ORANGE CAPRACYL BROWN HRN (1) ACID ORANGE GG CRYSTALS (1)ACRIDINE ORANGE 10-NONYL BROMIDE (2) AMANIL FAST ORANGE ER (1) AMIDINEFAST ORANGE 2 RL (1) ANTHANOL CHROME ORANGE R (1) ASTRAZON ORANGE G (1)ASTRAZON ORANGE R (1) AZOANTHRENE GOLDEN ORANGE R (1) BASIC ORANGE 21(GENACRYL ORANGE G) (1) BASIC ORANGE 22 (GENACRYL ORANGE R) (1) BASICORANGE 24 (SEVRON ORANGE L) (1) BASIC ORANGE 25 (SEVRON ORANGE CL) (1)BASIC ORANGE 26 (SEVRON BROWN YL) (1) BASIC ORANGE 27 (ASTRAZON ORANGE 3RL) (1) BASIC ORANGE 28 (ASTRAZON ORANGE RRL) (1) BASIC ORANGE 29(ASTRAZON GOLDEN YELLOW GLD) (1) BASIC ORANGE 30 (ASTRAZON YELLOW BROWN2 GL) (1) BASIC ORANGE 4-11(C.I. 46035) (1) BASIC ORANGE 43 (DEORLENEFAST ORANGE 2 GL) (1) BASIC ORANGE 54 (MAXILON ORANGE 4 RL EXTRA CONC.)(1) BENZANOL ORANGE R (1) BENZO FAST ORANGE 2 RL (1) BENZO FAST ORANGEWS (1) BENZYL ORANGE (1) BROMOCRESOL ORANGE (1) BUFFALO DIRECT ORANGE Y(1) C.I. 326 AMANIL FAST ORANGE S (1) C.I. 621 AMANIL FAST ORANGE CG (1)CALCO ACID ORANGE II (1) CALCOCHROME ORANGE R EXTRA CONC. (1) CALCOCIDFAST LIGHT ORANGE 2 G (1) CALCOCID MILLING ORANGE 4 R CONC. (1) CALCOCIDORANGE Y EXTRA CONC. (1) CALCODUR ORANGE EGL (1) CALCODUR ORANGE GL (1)CALCOFAST WOOL ORANGE 4 RN (1) CALCOFORM ORANGE 5 RE (1) CALCOLITE FASTORANGE 3 R (1) CALCOLOID FLAMING ORANGE 6 RD EXTRA CONC. (1) CALCOLOIDGOLDEN ORANGE 4 RD (1) CALCOLOID GOLDEN ORANGE GD EXTRA CONC. (1)CALCOLOID GOLDEN ORANGE RRTD EXTRA CONC. (1) CALCOLOID ORANGE RD EXTRACONC. (1) CALCOMET ORANGE G (1) CALCOMINE FAST ORANGE 2 RS EXTRA (1)CALCOMINE FAST ORANGE E3G (1) CALCOMINE FAST ORANGE EG (1) CALCOMINEFAST ORANGE ER (1) CALCOMINE ORANGE 2RS (1) CALCOMINE ORANGE R SPECIAL(1) CALCONESE BRILLIANT ORANGE GF CONC. (1) CALCONESE ORANGE 3 RC (1)CALCONESE ORANGE G (1) CALCOSOL GOLDEN ORANGE RRTP (1) CALCOSOL PRINTINGORANGE RY (1) CALCOZINE ORANGE RS (1) CALCOZINE ORANGE YC (1) CAMACYLBRILLIANT ORANGE JER (1) CAPRACYL ORANGE RP (1) CELACYL BRILLIANT ORANGE3 R (1) -HYDROXY-1,4-NAPHTHOQUINONE (1) CHRYSOIDINE G (2) SUDAN II (1)TROPAEOLIN 000 NO. 1 (1) TROPAEOLIN O (1) TROPAEOLIN O SODIUM SALT (1)TROPAEOLIN OO (1) THIOXINE ORANGE R (1) TOLUYLENE FAST ORANGE LX (1)VARINYL ORANGE DAC (1) VAT ORANGE 1 (C.I. 59105) (1) VAT ORANGE 24(PONSOL GOLDEN ORANGE 3 GND EXTRA) (1) VAT ORANGE 3 (C.I. 59300) (1) VATORANGE 7 (SOLANTHRENE BRILLIANT ORANGE FJRA) (1) VAT ORANGE 9 (C.I.59700) (1) VEGENTINE ORANGE CSW (1) VERANTHRENE GOLDEN ORANGE 3 G (1)SUDAN ORANGE G (2) SULFONINE ORANGE GS CONC. (1) SULPHUR ORANGE (1)SUPERLITE FAST ORANGE RT (1) SUPRAMINE ORANGE G (1) SUPRANOL ORANGE RA(1) TANNIN ORANGE (1) TECTILON ORANGE 2 RT (1) THIAZOLE ORANGE (2)SOLVENT ORANGE 1 (NEWPORT OIL YELLOW C.I. 11920) (1) SOLVENT ORANGE 20(AZOSOL FAST ORANGE RA) (1) SOLVENT ORANGE 23 (IOSOL ORANGE) (1) SRAGOLDEN ORANGE FSI POWDER (1) SRA GOLDEN ORANGE I POWDER (1) SRA LIGHTORANGE FSI (1) SRA ORANGE BL (1) SRA ORANGE I POWDER (1) SRA ORANGE IIPOWDER SODIUM4-(3-(2,4-DI-ME-PH-AZO)-2,4-DI-HO-PH-AZO)-BENZENESULFONATE(ACID ORANGE24 (1) SODIUM4-(4-(BENZYL-ET-AMINO)-PH-AZO)-2,5-DI-CL-BENZENESULFONATE(ACID ORANGE50) (1) SODIUM 5-(4-CL-PH-AZO)-6-HO-NAPHTHALENE-2-SULFONATE(ACID ORANGE31 C.I. 15995) (1) SOLOPHENYL ORANGE TGL (1) REACTIVE ORANGE 5 (CIBACRONBRILLIANT ORANGE GP) (1) REACTIVE ORANGE 68 (LANASOL ORANGE R) (1)REACTIVE ORANGE 70 (CIBACRON GOLDEN YELLOW RE) (1) REACTONE ORANGE G (1)RESIST ORANGE N (1) RESOLIN ORANGE 5 R (1) RORACYL ORANGE R (1)ROSANTHRENE ORANGE 3 R CONC. (1) ROSANTHRENE ORANGE RSS (1) SETACYLORANGE P-RFL (1) REACTIVE ORANGE 13 (PROCION ORANGE H-2R) (1) REACTIVEORANGE 16 (1) REACTIVE ORANGE 2 (CIBACRON BRILLIANT ORANGE 2G-E) (1)REACTIVE ORANGE 29 (LANASOL ORANGE G) (1) REACTIVE ORANGE 35 (CIBACRONORANGE 4 R-A) (1) REACTIVE ORANGE 44 (CIBACRON PRONT ORANGE G) (1)REACTIVE ORANGE 45 (CIBACRON PRONT GOLDEN YELLOW 2 R) (1) REACTIVEORANGE 46 (CIBACRON PRONT ORANGE BROWN 3 R) (1) PONTAMINE FAST ORANGE 2G CONC. (1) PONTAMINE FAST ORANGE MR (1) PONTAMINE FAST ORANGE MRL (1)PONTAMINE FAST ORANGE RGL EXTRA CONC. (1) PONTAMINE FAST ORANGE S (1)PROCION ORANGE MX2R (1) PROCION ORANGE MXG (1) PYRAMINE ORANGE 3 G (1)PYRAMINE ORANGE R (1) PYRAZOL FAST ORANGE RL (1) POLYDYE HISPERSE ORANGE5 RH (1) POLYFORM ORANGE RF EXTRA CONC. (1) POLYPROPYLENE ORANGE Y (1)PONSOL BRILLIANT ORANGE RKD EXTRA CONC. (1) PONSOL GOLDEN ORANGE 4 RDEXTRA CONC. (1) PONSOL GOLDEN ORANGE G EXTRA CONC. (1) PONSOL GOLDENORANGE GD EXTRA CONC. (1) PONSOL GOLDEN ORANGE RRTD EXTRA CONC. (1)PONTACHROME ORANGE 4 G (1) PONTACHROME ORANGE RL (1) PARA BRILLIANTORANGE G (1) PARANOL FAST ORANGE EG (1) PARANOL FAST ORANGE ER (1)PARANOL FAST ORANGE GL (1) POLAR ORANGE R CONC. (1) POLY(DISPERSE ORANGE3 ACRYLAMIDE) (1) POLY(DISPERSE ORANGE 3 METHACRYLAMIDE) (1) POLY[METHYLMETHACRYLATE-CO-(DISPERSE ORANGE 3 ACRYLAMIDE)] (1) POLY[METHYLMETHACRYLATE-CO-(DISPERSE ORANGE 3 METHACRYLAMIDE)] (1) ORANGE G (5)ORANGE G SOLUTION (1) ORANGE GG (1) ORANGE GS (1) MORDANT ORANGE 34(CHROMAVEN BRILLIANT ORANGE 2 R) (1) MORDANT ORANGE 8 (OMEGA CHROMEORANGE ML) (1) NABOR ORANGE G (1) NABOR ORANGE R (1) NAPTHANIL ORANGE RBASE (1) NATIONAL CHROMOLAN ORANGE R (1) NATIONAL WOOL ORANGE A CONC.(1) NATURAL YELLOW 8, 11 (ANRANTINE OSAGE ORANGE C.I. 75660) (1)NEUTRACYL ORANGE R (1) NEUTRAL ORANGE O (1), wherein the orange dye ispresent in a concentration in the range of about 0.001% to 10% byweight.
 9. A lens according to claim 8 wherein the orange dye is presentin the range of about 0.002% to about 5% by weight.
 10. A lens accordingto claim 8 wherein the orange dye is present in the range of about0.003% to about 3% by weight.
 11. An intraocular lens comprising acopolymer of an ophthalmic device base monomer and a polymerizableorange dye, the orange dye having a coefficient of extinction (“e”) ofat least 1500 M-¹ cm-¹ for a region between 350 nanometers and 500 nmand being present in a concentration range of about 0.001% to about 10%by weight.
 12. A lens according to claim 11 wherein the orange dye hasan “e” of at least 3000 M-¹ cm-¹.
 13. A lens according to claim 11wherein the orange dye has an “e” of at least 5000 M-¹ cm-¹.
 14. A lensaccording to claim 11 wherein the orange dye is present at aconcentration in the range of about 0.02% to about 5% by weight.
 15. Alens according to claim 11 wherein the orange dye is present at aconcentration in the range of about 0.003% to about 3% by weight.
 16. Alens according to claim 11 wherein the orange dye is selected from thegroup consisting essentially of: disperse orange 3 acrylamide, disperseorange 3 methacrylamide, disperse orange 3 acrylate, disperse orange 3methacrylate, disperse orange 25 acrylamide, disperse orange 25methacrylamide, disperse orange 25 acrylate, disperse orange 25methacrylate, and 10-Dodecylacridine Orange Bromide, ACID ORANGE 12(CROCEINE ORANGE C.I. 15970) ACID ORANGE 128 (MERPACYL ORANGE R) (1)ACID ORANGE 132 (MERPACYL YELLOW AR) ACID ORANGE 19 (SUPRAMINE RED GGA)ACID ORANGE 2 B (1) ACID ORANGE 3 (C.I. 10385) (1) ACID ORANGE 33 (C.I.24780) (1) ACID ORANGE 34 (CHROMACYL ORANGE GR) (1) ACID ORANGE 43(XYLENE FAST ORANGE P) (1) ACID ORANGE 47 (BENZYL FAST ORANGE G) (1)ACID ORANGE 5 (ACID YELLOW D C.I. 13080) (1) ACID ORANGE 51 (1) ACIDORANGE 60 (CAPRACYL ORANGE R) (1) ACID ORANGE 62 (NEOLAN ORANGE GRE) (1)ACID ORANGE 63 ACID ORANGE 63 (POLAR YELLOW R OR SUPRANOL YELLOW RA) (1)ACID ORANGE 64 (CAPRACYL YELLOW 3 RD) (1) ACID ORANGE 74 (1) ACID ORANGE74 (NEOLAN ORANGE G OR GYCOLAN ORANGE GL) (1) ACID ORANGE 79 (C.I.23255) (1) ACID ORANGE 8 (1) ACID ORANGE 86 (IRGALAN ORANGE RL) (1) ACIDORANGE 87 (CIBALAN YELLOW 2 BRL) (1) ACID ORANGE 94 (IRGANOL ORANGEGRLS) (1) ACID ORANGE CAPRACYL BROWN HRN (1) ACID ORANGE GG CRYSTALS (1)ACRIDINE ORANGE 10-NONYL BROMIDE (2) AMANIL FAST ORANGE ER (1) AMIDINEFAST ORANGE 2 RL (1) ANTHANOL CHROME ORANGE R (1) ASTRAZON ORANGE G (1)ASTRAZON ORANGE R (1) AZOANTHRENE GOLDEN ORANGE R (1) BASIC ORANGE 21(GENACRYL ORANGE G) (1) BASIC ORANGE 22 (GENACRYL ORANGE R) (1) BASICORANGE 24 (SEVRON ORANGE L) (1) BASIC ORANGE 25 (SEVRON ORANGE CL) (1)BASIC ORANGE 26 (SEVRON BROWN YL) (1) BASIC ORANGE 27 (ASTRAZON ORANGE 3RL) (1) BASIC ORANGE 28 (ASTRAZON ORANGE RRL) (1) BASIC ORANGE 29(ASTRAZON GOLDEN YELLOW GLD) (1) BASIC ORANGE 30 (ASTRAZON YELLOW BROWN2 GL) (1) BASIC ORANGE 4-11(C.I. 46035) (1) BASIC ORANGE 43 (DEORLENEFAST ORANGE 2 GL) (1) BASIC ORANGE 54 (MAXILON ORANGE 4 RL EXTRA CONC.)(1) BENZANOL ORANGE R (1) BENZO FAST ORANGE 2 RL (1) BENZO FAST ORANGEWS (1) BENZYL ORANGE (1) BROMOCRESOL ORANGE (1) BUFFALO DIRECT ORANGE Y(1) C.I. 326 AMANIL FAST ORANGE S (1) C.I. 621 AMANIL FAST ORANGE CG (1)CALCO ACID ORANGE II (1) CALCOCHROME ORANGE R EXTRA CONC. (1) CALCOCIDFAST LIGHT ORANGE 2 G (1) CALCOCID MILLING ORANGE 4 R CONC. (1) CALCOCIDORANGE Y EXTRA CONC. (1) CALCODUR ORANGE EGL (1) CALCODUR ORANGE GL (1)CALCOFAST WOOL ORANGE 4 RN (1) CALCOFORM ORANGE 5 RE (1) CALCOLITE FASTORANGE 3 R (1) CALCOLOID FLAMING ORANGE 6 RD EXTRA CONC. (1) CALCOLOIDGOLDEN ORANGE 4 RD (1) CALCOLOID GOLDEN ORANGE GD EXTRA CONC. (1)CALCOLOID GOLDEN ORANGE RRTD EXTRA CONC. (1) CALCOLOID ORANGE RD EXTRACONC. (1) CALCOMET ORANGE G (1) CALCOMINE FAST ORANGE 2 RS EXTRA (1)CALCOMINE FAST ORANGE E3G (1) CALCOMINE FAST ORANGE EG (1) CALCOMINEFAST ORANGE ER (1) CALCOMINE ORANGE 2RS (1) CALCOMINE ORANGE R SPECIAL(1) CALCONESE BRILLIANT ORANGE GF CONC. (1) CALCONESE ORANGE 3 RC (1)CALCONESE ORANGE G (1) CALCOSOL GOLDEN ORANGE RRTP (1) CALCOSOL PRINTINGORANGE RY (1) CALCOZINE ORANGE RS (1) CALCOZINE ORANGE YC (1) CAMACYLBRILLIANT ORANGE JER (1) CAPRACYL ORANGE RP (1) CELACYL BRILLIANT ORANGE3 R (1) -HYDROXY-1,4-NAPHTHOQUINONE (1) CHRYSOIDINE G (2) SUDAN II (1)TROPAEOLIN 000 NO. 1 (1) TROPAEOLIN O (1) TROPAEOLIN O SODIUM SALT (1)TROPAEOLIN OO (1) THIOXINE ORANGE R (1) TOLUYLENE FAST ORANGE LX (1)VARINYL ORANGE DAC (1) VAT ORANGE 1 (C.I. 59105) (1) VAT ORANGE 24(PONSOL GOLDEN ORANGE 3 GND EXTRA) (1) VAT ORANGE 3 (C.I. 59300) (1) VATORANGE 7 (SOLANTHRENE BRILLIANT ORANGE FJRA) (1) VAT ORANGE 9 (C.I.59700) (1) VEGENTINE ORANGE CSW (1) VERANTHRENE GOLDEN ORANGE 3 G (1)SUDAN ORANGE G (2) SULFONINE ORANGE GS CONC. (1) SULPHUR ORANGE (1)SUPERLITE FAST ORANGE RT (1) SUPRAMINE ORANGE G (1) SUPRANOL ORANGE RA(1) TANNIN ORANGE (1) TECTILON ORANGE 2 RT (1) THIAZOLE ORANGE (2)SOLVENT ORANGE 1 (NEWPORT OIL YELLOW C.I. 11920) (1) SOLVENT ORANGE 20(AZOSOL FAST ORANGE RA) (1) SOLVENT ORANGE 23 (IOSOL ORANGE) (1) SRAGOLDEN ORANGE FSI POWDER (1) SRA GOLDEN ORANGE I POWDER (1) SRA LIGHTORANGE FSI (1) SRA ORANGE BL (1) SRA ORANGE I POWDER (1) SRA ORANGE IIPOWDER SODIUM4-(3-(2,4-DI-ME-PH-AZO)-2,4-DI-HO-PH-AZO)-BENZENESULFONATE(ACID ORANGE24 (1) SODIUM4-(4-(BENZYL-ET-AMINO)-PH-AZO)-2,5-DI-CL-BENZENESULFONATE(ACID ORANGE50) (1) SODIUM 5-(4-CL-PH-AZO)-6-HO-NAPHTHALENE-2-SULFONATE(ACID ORANGE31 C.I. 15995) (1) SOLOPHENYL ORANGE TGL (1) REACTIVE ORANGE 5 (CIBACRONBRILLIANT ORANGE GP) (1) REACTIVE ORANGE 68 (LANASOL ORANGE R) (1)REACTIVE ORANGE 70 (CIBACRON GOLDEN YELLOW RE) (1) REACTONE ORANGE G (1)RESIST ORANGE N (1) RESOLIN ORANGE 5 R (1) RORACYL ORANGE R (1)ROSANTHRENE ORANGE 3 R CONC. (1) ROSANTHRENE ORANGE RSS (1) SETACYLORANGE P-RFL (1) REACTIVE ORANGE 13 (PROCION ORANGE H-2R) (1) REACTIVEORANGE 16 (1) REACTIVE ORANGE 2 (CIBACRON BRILLIANT ORANGE 2G-E) (1)REACTIVE ORANGE 29 (LANASOL ORANGE G) (1) REACTIVE ORANGE 35 (CIBACRONORANGE 4 R-A) (1) REACTIVE ORANGE 44 (CIBACRON PRONT ORANGE G) (1)REACTIVE ORANGE 45 (CIBACRON PRONT GOLDEN YELLOW 2 R) (1) REACTIVEORANGE 46 (CIBACRON PRONT ORANGE BROWN 3 R) (1) PONTAMINE FAST ORANGE 2G CONC. (1) PONTAMINE FAST ORANGE MR (1) PONTAMINE FAST ORANGE MRL (1)PONTAMINE FAST ORANGE RGL EXTRA CONC. (1) PONTAMINE FAST ORANGE S (1)PROCION ORANGE MX2R (1) PROCION ORANGE MXG (1) PYRAMINE ORANGE 3 G (1)PYRAMINE ORANGE R (1) PYRAZOL FAST ORANGE RL (1) POLYDYE HISPERSE ORANGE5 RH (1) POLYFORM ORANGE RF EXTRA CONC. (1) POLYPROPYLENE ORANGE Y (1)PONSOL BRILLIANT ORANGE RKD EXTRA CONC. (1) PONSOL GOLDEN ORANGE 4 RDEXTRA CONC. (1) PONSOL GOLDEN ORANGE G EXTRA CONC. (1) PONSOL GOLDENORANGE GD EXTRA CONC. (1) PONSOL GOLDEN ORANGE RRTD EXTRA CONC. (1)PONTACHROME ORANGE 4 G (1) PONTACHROME ORANGE RL (1) PARA BRILLIANTORANGE G (1) PARANOL FAST ORANGE EG (1) PARANOL FAST ORANGE ER (1)PARANOL FAST ORANGE GL (1) POLAR ORANGE R CONC. (1) POLY(DISPERSE ORANGE3 ACRYLAMIDE) (1) POLY(DISPERSE ORANGE 3 METHACRYLAMIDE) (1) POLY[METHYLMETHACRYLATE-CO-(DISPERSE ORANGE 3 ACRYLAMIDE)] (1) POLY[METHYLMETHACRYLATE-CO-(DISPERSE ORANGE 3 METHACRYLAMIDE)] (1) ORANGE G (5)ORANGE G SOLUTION (1) ORANGE GG (1) ORANGE GS (1) MORDANT ORANGE 34(CHROMAVEN BRILLIANT ORANGE 2 R) (1) MORDANT ORANGE 8 (OMEGA CHROMEORANGE ML) (1) NABOR ORANGE G (1) NABOR ORANGE R (1) NAPTHANIL ORANGE RBASE (1) NATIONAL CHROMOLAN ORANGE R (1) NATIONAL WOOL ORANGE A CONC.(1) NATURAL YELLOW 8, 11 (ANRANTINE OSAGE ORANGE C.I. 75660) (1)NEUTRACYL ORANGE R (1) NEUTRAL ORANGE O (1).